Tips for Managing a Remote Sales Team

As a modern sales leader, there will be times you need to manage a remote sales team. Now is likely one of those times.

If you have the good fortune of leading an established sales organization you will probably make a smooth transition to working from home. In that case, this article probably isn’t for you. You know your benchmarks, you know your team, and your team knows the playbook. You have tools in place for sales efficiency and tracking. You know what to measure and you know how to spot trouble and solve for it early. You are a well-oiled machine that just happens to need to work remotely (for whatever reason from an office move that temporarily has everyone at home for a week to a global pandemic that forces everyone home indefinitely). 

Managing a nascent sales team remotely is quite different and can feel challenging and murky. If you are building a sales team you may not have enough benchmarks to measure against. You may have all sorts of ramping reps in various stages of readiness. You may not yet have playbooks to draw on. 

How will you know what’s working and what isn’t? How will you know who is working and who isn’t? How will you know if you have a skill problem, a training problem, a market problem, a lead problem or any other variety of issues? It’s hard enough to know how you are really doing when you are in the throes of scaling a nascent sales organization, let alone one that’s been sent home to work remotely for the first time.

Hard, but definitely not impossible. Here are a few tips to help you along the way. 

Morning stand-up & commit.

A remote sales team should meet each morning for a 15-minute meeting (with video on!). If the team is large enough you may need several different stand-ups—one for SDRs, one for enterprise reps, etc.

The morning stand-up is a great time to run through a quick skill refresher or discuss a tidbit of company news. And it’s also important to have each person make a commitment to the group. Commits may range from how many calls an SDR is going to make to which deal a rep is going to move forward in the pipeline. Everyone makes an activity or outcome-based commit during morning standup.

Afternoon recap & reflection.

In the afternoon, the team should come back together for a 15-minute stand-up to discuss their day, recap accomplishments and report on their commit. This is also a great time to share tips, new talk tracks and collaborate on things that came up throughout the day.

The daily rituals of morning and afternoon standups are important in a nascent sales team because a remote team doesn’t get the benefit of ad hoc coaching, collaboration, and discussion that naturally happens on the sales floor.

Visible activity and outcomes.

A challenge with a remote team can be visibility into key metrics, so it’s important to find a way to keep activity and outcomes visible and top of mind. In an office environment, I love a sales wall, and in a remote environment, you need to find a way to replicate that and reference it often as a team. There are tools that can do this and automatically post data to Slack. Or you can have a sales admin manually do it. Even better, have the team post their results throughout the day and then push out the formal dashboard and metrics in the afternoon.

There is nothing like the excitement and energy of a Slack channel filled with updates from reps on closed-won deals, new opportunities opened, revenue booked, etc.

A modern sales stack.

You can’t manage any sales team—let alone a remote one—without the right tools in place. At a minimum (without naming any brands):

• CRM
• Video conferencing
• Inter-office chat
• Call recording
• Real-time dashboards
• List building and prospecting
• Sales cadence  
• Commission tracking
• Playbook software

Playbooks, playbooks, playbooks.

If your sales organization is so nascent that you don’t have sales playbooks, create some fast. Playbooks give everyone a common point of reference, help ensure consistency and uniformity and will help you ramp reps more quickly.

If you do already have playbooks make sure you are referencing them often and keeping them up to date. I’ve got tons of sales playbook resources here.

The right culture.

Sales culture is so important. Your team needs to be clear on your culture, and how to embody it. It starts with you modeling it and reinforcing it frequently. In a remote environment, things like accountability, transparency, visibility, communication and trust are most important.

The right meetings.

There’s never time to have meetings for meeting’s sake. Every sales meeting needs to have purpose and be valuable for the reps.

Make sure you are having frequent one-on-one’s and skip levels.  Thoughtfully weave in team meetings like deal strategy lunch sessions, breakfast forecast meetings and fun role-play sessions. Whatever normal meeting cadence you would have in an office environment translates well to a remote environment.

You may be thinking that two standups a day, one on one’s, skip levels and team meetings will result in a day just jam-packed with meetings. First, there aren’t really any additional meetings here than you would have in an office environment. They are just all the more important in a remote environment. And, there is no need to be dogmatic about what’s recommended here. Adapt and create a meeting schedule that works well for your team. Maybe stand-ups happen Tuesday, Wednesday, Thursday, for example. Maybe you do ‘happy hour’ deal strategy on Friday afternoons when everyone is winding down productivity anyway.

In a remote environment, you need to ‘see’ your people often and have a discipline around keeping meetings because you don’t have the “on the floor” energy. But you also need to balance that by designing a schedule that works well and maximizes rep productivity. This is especially true when you have reps in different time zones.

Rituals and continuity.

If you had rituals in the office, like hitting the gong every time a sale is made, find a way to continue those rituals remotely. If your team is so new that your rituals were just forming, don’t put that aspect of your sales culture on hold. Create rituals if you don’t have them yet. Rituals help bind us together and create a sense of community. This can be just as strong remote as it is in-person.

Communication.

It probably goes without saying that communication is key. But, even in an office environment, it’s hard to get communication right when your company is growing quickly.

For remote communication, context becomes even more important. So does repetition. Communicate something in a meeting, then reinforce it in a quick email, then post it in a Slack message, and then bring it back up again some other way in a few days or weeks. While you may think that’s overkill, it’s not. People retain information differently, or someone may be distracted the first time you communicate something. Over-communicate, frequently and on repeat.

For context, be a storyteller, provide background and supporting information or relevant details whenever possible.

The right people.

Hire well. Hire well. Hire well. I can’t stress this one enough. In a remote environment, you need to have a team of professionals who you trust, who communicate well, who value transparency and who hustle independently with a lot of drive & grit on their own.

If you don’t trust your people, you hired the wrong people…and that’s a much bigger problem.

If you are doubting someone’s skill, work with them until you are certain they either have the skills or they don’t. If you are doubting that someone is putting in the work increase the measurement & oversight of that person until you are confident in what they are (or aren’t) producing. If you have ramping reps, leverage your playbooks and tools to train and coach them with a 30/60/90 sales ramp plan that you actually stick to.

Don’t hang out in a world of doubt about your people. That’s a lot of wasted energy and brain cells. But, it starts with hiring the right team of professionals and building trust quickly through communication, transparency, productivity and ultimately results.

Lean into remote.

Nothing beats the energy of a startup office’s sales floor. Even as a big fan of remote work, I know that to be true. But if you find yourself managing a remote sales team for the first time, lean into it and embrace the benefits of remote work, rather than lament the loss of office face time.

Plenty of startups successfully run fully remote sales teams. Approach it with best practices and creativity and you can succeed with a remote sales culture no matter your stage or current environment.